Synthesis and properties of optically active substituted polyacetylenes having carboxyl and/or amino groups

Polyacetylenes having carboxyl and/or amino groups in the side chain were synthesized by the polymerization of N-(2-propynyloxycarbonyl)-l-alanine (1) and l-alanine N-propargylamide (2) catalyzed with a rhodium cation complex. Poly(10.5-co-20.5) exhibited a larger CD signal than the homopolymers. The polymer mixtures obtained by the polymerization of 1 in the presence of poly(2), and those obtained by the polymerization of 2 in the presence of poly(1) showed specific rotations larger than calculated. The polymerization of propargylamine in the presence of poly(1) did not exhibit significant effect, while the polymer mixtures obtained by the polymerization of propiolic acid in the presence of poly(2) exhibited [α]D of positive sign, although poly(2) alone exhibited [α]D of negative sign.